I don't find even this split worth my time, even as a listing, on my last rental listing I was stood up well over a dozen times last minute!

As you know, a lot of STRs claims are pretty small so they don’t worth putting a claim and increasing your insurance premium for your portfolio. $100 per month is a pretty significant amount considering the volume.

The financial of property is good:      DSCR = 1.3; LTV = 45%;Both my liquidity and net worth passes Chase's test.

With limited time I have in US, I have some financial targets to meet, one being scale and increase my net worth.

Sometimes cities will allow this, but it depends on local zoning rules.If neither option works, it might be worth consulting a real estate attorney to explore your options.

I find that most of the time, paying points up front isn't worth it in the end.

net worth check..

Did your discount make it worth your time to buy it anyways? 

I've been bringing in $400k worth of business but its not enough here in California that I keep to really make a difference.

If it was owned by someone famous, and its provenance can be demonstrated, then yes, it is worth more.